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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/50/1545067.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1545067
loop_
_publ_author_name
'Maury, Julien'
'Zawodny, Wojciech'
'Clayden, Jonathan'
_publ_section_title
;
 Stereospecific Intramolecular Arylation of 2- and 3-Pyridyl Substituted
 Alkylamines via Configurationally Stable α-Pyridyl Organolithiums.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              472
_journal_page_last               475
_journal_paper_doi               10.1021/acs.orglett.6b03603
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H18 Cl N3 O'
_chemical_formula_weight         303.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.54450(10)
_cell_length_b                   9.1514(2)
_cell_length_c                   19.7296(4)
_cell_measurement_reflns_used    7355
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      4.48
_cell_volume                     1542.74(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18119
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.143
_diffrn_reflns_theta_min         4.482
_exptl_absorpt_coefficient_mu    2.207
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.767605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1182 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.031(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0314P)²+0.2253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0623
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2918
_reflns_number_total             3026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b03603_si_002.cif
_cod_data_source_block           s4554ma
_cod_depositor_comments          'Adding full bibliography for 1545067.cif.'
_cod_database_code               1545067
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.608
_shelx_estimated_absorpt_t_max   0.843
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.7146(2) 0.1284(2) 0.19768(10) 0.0173(4) Uani 1 1 d . .
C2 C 0.6616(2) 0.0844(2) 0.26918(10) 0.0169(4) Uani 1 1 d . .
C3 C 0.7217(2) -0.0389(2) 0.30153(10) 0.0187(4) Uani 1 1 d . .
H3 H 0.7952 -0.0985 0.2782 0.022 Uiso 1 1 calc R U
C4 C 0.6773(2) -0.0769(2) 0.36662(10) 0.0195(4) Uani 1 1 d . .
H4 H 0.7191 -0.1616 0.3878 0.023 Uiso 1 1 calc R U
C5 C 0.5705(2) 0.0111(2) 0.40047(10) 0.0200(4) Uani 1 1 d . .
C6 C 0.5063(2) 0.1331(2) 0.37015(10) 0.0220(4) Uani 1 1 d . .
H6 H 0.4323 0.1917 0.3937 0.026 Uiso 1 1 calc R U
C7 C 0.5516(2) 0.1684(2) 0.30472(10) 0.0205(4) Uani 1 1 d . .
H7 H 0.5070 0.2517 0.2834 0.025 Uiso 1 1 calc R U
C8 C 0.8786(2) -0.0782(2) 0.15665(10) 0.0164(4) Uani 1 1 d . .
C9 C 1.0365(2) -0.2652(2) 0.10352(10) 0.0221(4) Uani 1 1 d . .
H9A H 0.9853 -0.3417 0.1303 0.033 Uiso 1 1 calc R U
H9B H 1.1472 -0.2898 0.0973 0.033 Uiso 1 1 calc R U
H9C H 0.9856 -0.2578 0.0592 0.033 Uiso 1 1 calc R U
C10 C 1.0104(2) 0.1363(2) 0.20621(10) 0.0207(4) Uani 1 1 d . .
H10A H 1.0861 0.0626 0.2212 0.031 Uiso 1 1 calc R U
H10B H 0.9831 0.1998 0.2444 0.031 Uiso 1 1 calc R U
H10C H 1.0565 0.1951 0.1698 0.031 Uiso 1 1 calc R U
C11 C 0.5950(2) 0.0876(2) 0.14262(10) 0.0175(4) Uani 1 1 d . .
C12 C 0.4424(2) 0.0469(2) 0.15666(10) 0.0183(4) Uani 1 1 d . .
H12 H 0.4121 0.0401 0.2029 0.022 Uiso 1 1 calc R U
C13 C 0.3789(2) 0.0250(3) 0.04459(11) 0.0278(4) Uani 1 1 d . .
H13 H 0.3053 0.0007 0.0103 0.033 Uiso 1 1 calc R U
C14 C 0.5275(3) 0.0680(2) 0.02525(11) 0.0302(5) Uani 1 1 d . .
H14 H 0.5546 0.0743 -0.0214 0.036 Uiso 1 1 calc R U
C15 C 0.6356(2) 0.1014(2) 0.07472(11) 0.0254(4) Uani 1 1 d . .
H15 H 0.7374 0.1337 0.0625 0.030 Uiso 1 1 calc R U
C16 C 0.7300(2) 0.2977(2) 0.19346(11) 0.0217(4) Uani 1 1 d . .
H16A H 0.7869 0.3337 0.2332 0.033 Uiso 1 1 calc R U
H16B H 0.6254 0.3417 0.1923 0.033 Uiso 1 1 calc R U
H16C H 0.7872 0.3243 0.1522 0.033 Uiso 1 1 calc R U
Cl1 Cl 0.51484(6) -0.03342(6) 0.48279(2) 0.02893(13) Uani 1 1 d . .
N1 N 0.86935(17) 0.06370(17) 0.18119(8) 0.0166(3) Uani 1 1 d . .
N2 N 1.02363(19) -0.12592(17) 0.13887(8) 0.0175(3) Uani 1 1 d . .
N3 N 0.33449(18) 0.01631(19) 0.10925(9) 0.0227(4) Uani 1 1 d . .
O1 O 0.76290(15) -0.15704(14) 0.15236(8) 0.0223(3) Uani 1 1 d . .
H2 H 1.095(3) -0.069(3) 0.1337(12) 0.020(6) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 111.08(15)
N1 C1 C11 109.91(15)
C2 C1 C11 112.92(15)
N1 C1 C16 108.06(15)
C2 C1 C16 109.54(16)
C11 C1 C16 105.04(15)
C3 C2 C7 117.49(18)
C3 C2 C1 121.59(16)
C7 C2 C1 120.92(17)
C4 C3 C2 121.82(17)
C4 C3 H3 119.1
C2 C3 H3 119.1
C3 C4 C5 118.74(18)
C3 C4 H4 120.6
C5 C4 H4 120.6
C6 C5 C4 121.47(19)
C6 C5 Cl1 119.02(15)
C4 C5 Cl1 119.51(15)
C5 C6 C7 118.78(18)
C5 C6 H6 120.6
C7 C6 H6 120.6
C6 C7 C2 121.67(18)
C6 C7 H7 119.2
C2 C7 H7 119.2
O1 C8 N2 121.84(17)
O1 C8 N1 121.91(17)
N2 C8 N1 116.24(16)
N2 C9 H9A 109.5
N2 C9 H9B 109.5
H9A C9 H9B 109.5
N2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C15 116.92(18)
C12 C11 C1 123.38(18)
C15 C11 C1 119.54(17)
N3 C12 C11 124.31(19)
N3 C12 H12 117.8
C11 C12 H12 117.8
N3 C13 C14 122.83(19)
N3 C13 H13 118.6
C14 C13 H13 118.6
C15 C14 C13 118.9(2)
C15 C14 H14 120.5
C13 C14 H14 120.5
C14 C15 C11 119.65(19)
C14 C15 H15 120.2
C11 C15 H15 120.2
C1 C16 H16A 109.5
C1 C16 H16B 109.5
H16A C16 H16B 109.5
C1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C8 N1 C10 119.74(15)
C8 N1 C1 119.99(15)
C10 N1 C1 118.62(14)
C8 N2 C9 118.23(16)
C8 N2 H2 121.2(17)
C9 N2 H2 116.3(18)
C13 N3 C12 117.29(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.485(2)
C1 C2 1.535(3)
C1 C11 1.537(3)
C1 C16 1.558(2)
C2 C3 1.395(3)
C2 C7 1.402(3)
C3 C4 1.384(3)
C3 H3 0.9500
C4 C5 1.388(3)
C4 H4 0.9500
C5 C6 1.380(3)
C5 Cl1 1.741(2)
C6 C7 1.386(3)
C6 H6 0.9500
C7 H7 0.9500
C8 O1 1.227(2)
C8 N2 1.360(2)
C8 N1 1.388(2)
C9 N2 1.457(2)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 N1 1.462(2)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.384(3)
C11 C15 1.390(3)
C12 N3 1.343(3)
C12 H12 0.9500
C13 N3 1.333(3)
C13 C14 1.383(3)
C13 H13 0.9500
C14 C15 1.379(3)
C14 H14 0.9500
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
N2 H2 0.81(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O1 0.95 2.35 3.029(2) 128.0 3_655
C13 H13 Cl1 0.95 2.80 3.579(2) 139.3 4_554
N2 H2 N3 0.81(3) 2.24(3) 3.015(2) 160(2) 1_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 C2 C3 -21.7(2)
C11 C1 C2 C3 102.36(19)
C16 C1 C2 C3 -140.96(18)
N1 C1 C2 C7 157.63(16)
C11 C1 C2 C7 -78.4(2)
C16 C1 C2 C7 38.3(2)
C7 C2 C3 C4 -1.0(3)
C1 C2 C3 C4 178.32(17)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C6 1.3(3)
C3 C4 C5 Cl1 -179.23(14)
C4 C5 C6 C7 -0.8(3)
Cl1 C5 C6 C7 179.69(15)
C5 C6 C7 C2 -0.6(3)
C3 C2 C7 C6 1.5(3)
C1 C2 C7 C6 -177.85(17)
N1 C1 C11 C12 138.50(17)
C2 C1 C11 C12 13.8(2)
C16 C1 C11 C12 -105.5(2)
N1 C1 C11 C15 -46.3(2)
C2 C1 C11 C15 -170.93(17)
C16 C1 C11 C15 69.8(2)
C15 C11 C12 N3 2.0(3)
C1 C11 C12 N3 177.35(17)
N3 C13 C14 C15 0.9(3)
C13 C14 C15 C11 1.7(3)
C12 C11 C15 C14 -3.1(3)
C1 C11 C15 C14 -178.61(19)
O1 C8 N1 C10 159.99(18)
N2 C8 N1 C10 -18.8(2)
O1 C8 N1 C1 -5.2(3)
N2 C8 N1 C1 176.07(17)
C2 C1 N1 C8 83.8(2)
C11 C1 N1 C8 -41.9(2)
C16 C1 N1 C8 -156.03(17)
C2 C1 N1 C10 -81.6(2)
C11 C1 N1 C10 152.74(16)
C16 C1 N1 C10 38.6(2)
O1 C8 N2 C9 10.3(3)
N1 C8 N2 C9 -170.96(16)
C14 C13 N3 C12 -2.1(3)
C11 C12 N3 C13 0.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139049508
